Total synthesis and assignment of the absolute configuration of (+)-omphalic acid
R Chen, D Qiu, X Lei, Y Niu, Y Hua, H Peng… - Organic …, 2021 - ACS Publications
R Chen, D Qiu, X Lei, Y Niu, Y Hua, H Peng, T Zeng, Y Zhang
Organic Letters, 2021•ACS PublicationsOmphalane diterpenoids usually contain a cyclohexane-fused bicyclo [3.2. 1] octane
scaffold embedded with two continuous quaternary carbon centers, which pose
considerable challenges to synthetic chemists. Herein, we reported the first total synthesis of
omphalic acid with high stereochemical control, featuring an intermolecular Diels–Alder
cycloaddition, ring reorganization through Criegee oxidative cleavage and programmed
aldol condensations, conformationally controlled hydrogenation, and Pd-catalyzed …
scaffold embedded with two continuous quaternary carbon centers, which pose
considerable challenges to synthetic chemists. Herein, we reported the first total synthesis of
omphalic acid with high stereochemical control, featuring an intermolecular Diels–Alder
cycloaddition, ring reorganization through Criegee oxidative cleavage and programmed
aldol condensations, conformationally controlled hydrogenation, and Pd-catalyzed …
Omphalane diterpenoids usually contain a cyclohexane-fused bicyclo[3.2.1]octane scaffold embedded with two continuous quaternary carbon centers, which pose considerable challenges to synthetic chemists. Herein, we reported the first total synthesis of omphalic acid with high stereochemical control, featuring an intermolecular Diels–Alder cycloaddition, ring reorganization through Criegee oxidative cleavage and programmed aldol condensations, conformationally controlled hydrogenation, and Pd-catalyzed carboxylation. The absolute configuration of omphalic acid was defined for the first time via the asymmetric total synthesis facilitated by a derivatization resolution protocol.
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